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Cas Database

201856-53-3

201856-53-3

Identification

  • Product Name:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone

  • CAS Number: 201856-53-3

  • EINECS:

  • Molecular Weight:339.391

  • Molecular Formula: C20H21NO4

  • HS Code:

  • Mol File:201856-53-3.mol

Synonyms:2-Azetidinone,1-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-, [3R-(3a,4a)]-[partial]-;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:Crysdot
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one 95+%
  • Packaging:250mg
  • Price:$ 312
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one 95+%
  • Packaging:1g
  • Price:$ 780
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
  • Packaging:1 g
  • Price:$ 662.5
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
  • Packaging:250 mg
  • Price:$ 220
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
  • Packaging:100 mg
  • Price:$ 110
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
  • Packaging:50 mg
  • Price:$ 63
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
  • Packaging:500 mg
  • Price:$ 380
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(3R,4S)-1-BENZOYL-3-(2-ETHOXYETHOXYL)-4-PHENYL-2-AZETIDINONE 95.00%
  • Packaging:5MG
  • Price:$ 500.56
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  • Manufacture/Brand:Alichem
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one
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  • Manufacture/Brand:Alichem
  • Product Description:(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one
  • Packaging:250mg
  • Price:$ 340.08
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Relevant articles and documentsAll total 4 Articles be found

Method for preparation of taxol using an oxazinone

-

, (2008/06/13)

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: STR1 wherein R1 is aryl, heteroaryl, alkyl, alkenyl, alkynyl or OR7 wherein R7 is alkyl, alkenyl, a

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Ojima, Iwao,Habus, Ivan,Zhao, Mangzhu,Zucco, Martine,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry

, p. 6985 - 7012 (2007/10/02)

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.

Method for preparation of taxol using β-lactam

-

, (2008/06/13)

A β-lactam of the formula: STR1 wherein R1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R2 is hydrogen, alkyl, acyl, acetal, ethoxyethyl, or other hydroxyl protecting group; and R3 is aryl, substituted aryl, alky

Method for preparation of taxol using an oxazinone

-

, (2008/06/13)

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: STR1 wherein R1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R2 is hydrogen, ethoxyethyl, 2,2,2-tric

Process route upstream and downstream products

Process route

benzoyl chloride
98-88-4

benzoyl chloride

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 25 ℃; for 2h;
92%
With n-butyllithium; In tetrahydrofuran; hexane;
3.22 g (95%)
methanesulfonic acid
75-75-2,98527-29-8

methanesulfonic acid

benzoyl chloride
98-88-4

benzoyl chloride

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
With n-butyllithium; In tetrahydrofuran; hexane;
3.22 g (95%)
N-benzylidene-1,1,1-trimethylsilanamine
17599-61-0

N-benzylidene-1,1,1-trimethylsilanamine

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 100 percent / tetrahydrofuran / 2 h / 0 °C
4: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 4 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 100 percent / tetrahydrofuran / 2 h / 0 °C
4: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;
benzaldehyde
100-52-7

benzaldehyde

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 100 percent / tetrahydrofuran / 2 h / 0 °C
5: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 5 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 100 percent / tetrahydrofuran / 2 h / 0 °C
5: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 100 percent / tetrahydrofuran / 2 h / 0 °C
2: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; triethylamine; In tetrahydrofuran; dichloromethane;
3-Triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2,132201-31-1

3-Triisopropylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
2: 100 percent / tetrahydrofuran / 2 h / 0 °C
3: 92 percent / DMAP, triethylamine / CH2Cl2 / 2 h / 25 °C
With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 40 percent / NaH / tetrahydrofuran / 3 h / 35 °C
2: 88 percent / 0.5percent hydrochloric acid / ethanol / 48 h / 0 °C
With hydrogenchloride; sodium hydride; In tetrahydrofuran; ethanol;
(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

11(15->1)abeo-taxane-1,4,7,9-tetraacetoxy-10-benzoyloxy
153229-31-3

11(15->1)abeo-taxane-1,4,7,9-tetraacetoxy-10-benzoyloxy

C<sub>51</sub>H<sub>57</sub>NO<sub>16</sub>
184877-25-6

C51H57NO16

Conditions
Conditions Yield
(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone; 11(15->1)abeo-taxane-1,4,7,9-tetraacetoxy-10-benzoyloxy; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;
With hydrogenchloride; water; In tetrahydrofuran; at 0 - 20 ℃;
59%
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: hydrogenchloride / water; tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
With hydrogenchloride; sodium hexamethyldisilazane; In tetrahydrofuran; water;
C<sub>23</sub>H<sub>30</sub>O<sub>8</sub>

C23H30O8

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone
201856-53-3,133066-61-2

(3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone

C<sub>39</sub>H<sub>43</sub>NO<sub>11</sub>
1262663-14-8

C39H43NO11

Conditions
Conditions Yield
C23H30O8; (3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;
With hydrogenchloride; water; In tetrahydrofuran; at 0 - 20 ℃;
28%

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